Triethylsilane → ethyl 2-(5-cyclopentyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

HRID 1189537Notes

Reaction equation

HRID 1189537 reaction equation
[CH:1]1([C:6]2[N:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([CH3:11])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([SiH](CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[N:37]1([S:42]([C:45]2[CH:52]=[CH:51][CH:50]=[CH:49][C:46]=2[CH:47]=O)(=[O:44])=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38]1>ClCCl.[Au]>[CH:1]1([C:6]2[N:7]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]([CH3:11])=[C:9]([CH2:47][C:46]3[CH:49]=[CH:50][CH:51]=[CH:52][C:45]=3[S:42]([N:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)(=[O:43])=[O:44])[CH:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 573845822-(Pyrrolidin-1-ylsulfonyl)benzaldehydeHCID 67239192ethyl 2-(2-cyclopentyl-5-methyl-1H-pyrrol-1-yl)acetate

Product 1

HCID 53246982ethyl 2-(5-cyclopentyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetateYield 37.4%

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 6344DichloromethaneSolvent

Procedure

The general procedure was followed using ethyl 2-(2-cyclopentyl-5-methyl-1H-pyrrol-1-yl)acetate (3.49 g, 14.8 mmol), triethylsilane (7.11 mL, 44.5 mmol), trimethylsilyl trifluoromethanesulfonate (5.36 mL, 29.7 mmol), and 2-(pyrrolidin-1-ylsulfonyl)benzaldehyde (3.55 g, 14.8 mmol) in dichloromethane of (total volume: 170 ml). Purification on silica gel (Luknova 330 g, 20 mL/min) using 1 to 7% of a 7:1 acetonitrile/methanol solution in dichloromethane over 70 minutes afforded ethyl 2-(5-cyclopentyl-2-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (2.54 g, 5.54 mmol, 37% yield) as a viscous gold residue that was approximately 90% pure by 1H-NMR analysis, with the impurity being ethyl 2-(2-cyclopentyl-5-methyl-3-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate. 1H NMR (400 MHz, CDCl3) δ (ppm): 7.96 (dd, 1H), 7.40 (ddd, 1H), 7.22-7.28 (m, 2H, composite of two shifts), 4.56 (s, 2H), 4.23 (s, 2H), 4.18 (q, 2H), 3.28-3.31 (m, 4H), 2.83 (m, 1H), 2.03 (s, 3H), 1.89-1.99 (m, 3H), 1.84-1.88 (m, 4H), 1.49-1.74 (m, 5H, composite of multiple shifts), 1.29 (t, 3H).

Workup

  1. customPurification on silica gel (Luknova 330 g, 20 mL/min)
  2. customover 70 minutes

Sources & evidence

ORD record
ord-1c510494d04945e7bdf9e3dc20a29c4b
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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